The Battle of Charandaprash was an important milestone in the Black Company's campaign against the Shadowmasters. Croaker led an army of around 60,000 troops. The other legion commanders were Lady and the Prahbrindrah Drah of Taglios. Longshadow, who was the last of the Shadowmasters, had his forces commanded by the Company's traitors Mogaba and Blade. It took place on the Plain of Charandaprash, part of which was the only practical pass through the sprawling Dandha Presh mountain range.

The battle lasted for days. The most decisive moments was Blade's betrayal. He led a quarter of Longshadow’s army into a trap in which Croaker's army surrounded them and forced them to surrender and disarm. The trap had been laid months before by Croaker and Blade, when Croaker ordered Blade's defection in order to put somebody high ranking but reliable into Longshadow's military hierarchy. Longshadow, who was very unstable at that time (due to Kina's manipulation), panicked and ordered a retreat. Both his enemies and allies noted this to be a huge tactical mistake. He and his most important allies mounted Howler's flying carpet and tried to escape, sowing panic among his ranks. The carpet caught fire and almost crashed as it was fired upon by Croaker's carefully-placed soldiers using fireball projectors. They only escaped because a towering representation of the goddess Kina materialized without warning in order to save the Daughter of Night. Lady, whose sorcery was being restored to her, repelled the frightening apparition with the help of incoming fireballs that perforated it. The vision of Kina turned out to be the work of the unaligned wildcard Soulcatcher, and not the goddess herself at all.

Mogaba was badly hurt, but stayed and fought bravely. Finally, Lady used her sorcery, and Mogaba's army was forced to flee. The victors were too tired to pursue them, but many were picked off by Goblin's team, which had been placed on the far side of the Dandha Presh long beforehand. The decisive victory led to the Siege of Overlook.